Your technology partner for owner-run businesses.

Technology leadership, practical AI and digital marketing for businesses across Simcoe and Grey. One senior partner, from the first decision to the working result.

Book a free hour

Or call (705) 999-6126

ServicesExplore services

Chris Patten

18 years leading technology. Founder.
Based in Simcoe County.

Working across Simcoe & Grey Countiesheadwaydigital.ca

What I do.

From the first decision
to the working result.

Find your starting point

AI consultingagents & automation

Practical AI that takes routine work off your plate, with guardrails you approve.

See AI agents

Digital marketinglead generation & websites

More of the right customers find you and choose you.

See marketing and websites

Fractional CTO

Senior technology leadership, without a full-time hire.

See fractional CTO

Experience.

Client story

Placeholder: the lead client story goes here.

The client, the assignment and one verified result or approved quote. Awaiting Chris's choice before publishing.

18 years leading technology.

VP, IT and CIO from 1998 to 2016, then built and sold my own company. You work directly with me.

Meet Chris

Selected work.

FreshWagon

Online market for local food, delivered

ShoreGrade

Headway-operated web app for local business discovery and website report cards

Overhead Door

Lead generation

Seguin Property Care

Property maintenance services website

Field notesWhat small business owners need to know about AI

Bring one problem.
Leave with a next step.

One hour with me, at your business or by video, with a second look at your software costs if that helps. No sales pitch and nothing to fill in. If paid work makes sense, we agree scope and price before anything starts.

Book a free hour

Prefer to talk first? Call (705) 999-6126, message on WhatsApp or write to hello@headwaydigital.ca.

When you are ready to go further.

Specific projects

AI phone agent$1,500 setup, then from $499 a month
Website$4,000 to $8,000

See all services

Ongoing partnership

From $3,000 a month

Senior capacity reserved each month for priorities, delivery and the systems behind them.

See the partnership

Across Grey.
Across Simcoe.

Based in Simcoe County. On site across Simcoe and Grey.

Let's meet

On-site support across Simcoe County: Barrie, Collingwood, Creemore, Elmvale, Essa, Innisfil, Midland, Orillia, Oro-Medonte, Penetanguishene, Ramara, Severn, Springwater, Stayner, Tay, Tiny and Wasaga Beach. Across Grey County: Chatsworth, Georgian Bluffs, Grey Highlands, Hanover, Meaford, Owen Sound, Southgate, The Blue Mountains, Thornbury and West Grey. Book an on-site conversation.